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If you use the shell extension without putting the device in emergency connect mode you will not need to create the database manually (easyH10). If you do put the device in emergency connect mode (UMS) you will need to create the database manually either by using the rebuild database feature on the device or by using a program (easyH10).
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I've been having a similar experience with my H10. I just got it the other day and had to use UMS to load the las test firmware. I can sync regularWMA files that are on my PC, but for some reason I get an error message when I try to sync files that have been downloaded from pay sites. I have sync rights for these files but cannot burn them. Anyone have a solution?